As I was preparing to launch my new personalized Madeira itinerary planning service, I spent quite a bit of time going through the questions you guys regularly send me about planning trips to Madeira. And I realized that I keep seeing the same few things over and over again.

I’m not talking about the obvious Madeira itinerary advice you’ve probably already read a hundred times. Remember the micro climates. Plan your days by region. Don’t try to squeeze every major sight on the island into three days.

Instead, these are three mistakes that are a little less obvious — but can make a big difference to how relaxed and flexible your trip actually feels.

If you find my tips helpful and want to support my work, you can buy me a coffee here:
https://buymeacoffee.com/your_madeira

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1. Booking every hike months in advance

Yes, Madeira’s official PR trails require reservations. And yes, if there’s a popular hike you absolutely want to do at a specific time, you should book it early.

Right now, popular morning slots can sell out more than a month in advance, especially during the busy summer season. I’m hoping things will calm down a little once summer is over, but only time will tell.

This is particularly relevant for the most popular hikes. For example PR1 around Pico do Arieiro or PR6 to 25 Fontes. But that doesn’t mean you need to book every single hike before you even get on the plane.

The majority of Madeira’s PR trails don’t sell out that far in advance. For many of them, you’ll find enough availability to book the day before. At that point, you have a much better idea of the weather, how you’re feeling and what you actually want to do.

And remember: not every hike on Madeira is a PR trail.

There are plenty of beautiful non-PR hiking routes that don’t require a reservation at all. I recently hiked 100 miles of these trails for my 100 Miles of Trails series. There are endless trails and they are a great way to add some flexibility to a hiking-heavy itinerary.

My approach would therefore be:

Lock in the hikes that are genuine must-dos for you and likely to sell out. Leave the rest flexible.

Madeira’s weather changes. You might wake up to clouds in the mountains and beautiful sunshine somewhere else. You might be much more sore after yesterday’s hike than expected. Or you might simply decide that you’d rather spend the day at the beach.

There’s currently a lot of stress around Madeira’s PR trail reservations, but it really doesn’t need to dictate your entire trip.

2. Choosing your accommodation before thinking about your itinerary

It’s tempting to book your flights, find a nice hotel or apartment and then figure out what you’re going to do from there. But on Madeira, I’d actually think about the two together. The best place to stay depends quite a lot on what you want to do during your trip.

Funchal is a great all-around base. It’s particularly convenient if you don’t have a rental car, there are plenty of tours and activities departing from the city, you have restaurants and entertainment on your doorstep, and you’re well connected for exploring different parts of the island.

If you’re looking for warmer weather and beaches, you might prefer the southwest.

If hiking, nature and a little more peace and quiet are your priorities, the north might suit you really well. But it’s also not as conveniently connected to every other part of the island. If you’re planning to drive across Madeira in a different direction every single day, staying there for your entire trip might not make the most sense.

And if you’re here for longer, splitting your trip between two different bases can sometimes work really well.

There isn’t one “best” area to stay on Madeira. It depends on your activities, whether you’re renting a car, how much you want to drive, the type of atmosphere you enjoy and plenty of other personal preferences. So it’s best to think about those factors before locking in your accommodation.

But if you’re completely overwhelmed by the options, I personally think it’s pretty difficult to go very wrong with Funchal as your base.

3. Underestimating the driving — and not just the distances

Madeira is a small island, which can make it very tempting to look at a map and think: “We’ll just drive there.”

And technically, you probably can. But the driving itself is something I think a lot of itineraries underestimate.

Especially when you’ve just arrived, Madeira’s steep roads, winding mountain routes and narrow streets can take some getting used to. Even if you’re a confident driver at home, driving here can require a lot more concentration than you’re used to.

Now combine that with a hiking holiday. A four-hour hike can already leave you tired. Add two hours of driving on winding roads, and suddenly you’re exhausted.

Do you really want to do the same thing again the following morning?

I’d recommend balancing days with lots of driving with days where you stay closer to your accommodation or don’t need the car at all.

And if you’re not used to mountain roads, don’t necessarily make your biggest island road trip your first full day on Madeira. Start with places closer to where you’re staying, consider a guided tour for some of your exploring and give yourself a little time to get comfortable behind the wheel.

Save those longer road-trip days for once you’ve settled in.

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Bonus: Don’t wait until the end of your trip to book a guided tour

Whether it’s a guided hike, Jeep tour or walking tour, I’d actually recommend doing at least one toward the beginning of your trip rather than saving it for your final day.

First of all, it’s an easy way to explore without having to plan everything yourself or worry about driving.

But more importantly, you’ll spend a few hours with someone who knows Madeira. You’ll inevitably pick up tips, recommendations and little bits of local knowledge that you can use throughout the rest of your stay.

I guide hikes myself, and when I’m out with people toward the end of their trip, it happens surprisingly often that I’ll recommend a trail, restaurant or place and hear: “Damn, I wish we’d known that earlier.”

You can research Madeira for months before coming here — and you absolutely should do some research — but there’s only so much you can learn in advance.

First-hand recommendations from someone who actually lives on the island can help you adjust the rest of your plans and discover things you might otherwise have missed.

So if you’re planning to book a guided experience anyway, don’t leave it until your last day. And if a Jeep tour sounds right for you, I can’t recommend Desurbaniza-te enough. I’ve explored Madeira with them several times and they’re a great way to see some of the island’s less accessible spots without worrying about the driving yourself. You can also get 10% off with my code YOURMADEIRA.

Affiliate note: I may earn a small commission if you book using my code, at no extra cost to you.

Feeling overwhelmed by your Madeira itinerary?

For a relatively small island, planning a Madeira itinerary gets surprisingly complicated.

Which hikes do I book? How much driving is realistic? Where should you stay? Which activities make sense together? And how do you plan enough without making your itinerary so rigid that one rainy morning throws everything off?

That’s actually one of the reasons I recently launched my personalized Madeira trip planning service.

I’ll help you put together a trip based around your priorities while taking into account driving times, locations, reservations and enough flexibility for Madeira’s unpredictable weather. Because the goal isn’t to squeeze as much as physically possible into your holiday. It’s to plan a trip that you’ll actually enjoy once you’re here.